4-Fluorophenol → 4-(4-Fluorophenoxy)benzaldehyde

HRID 705838Notes

Reaction equation

HRID 705838 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 38568024-(4-Fluorophenoxy)benzaldehydeYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-fluorophenol (10 g, 89 mmol) and 4-fluorobenzaldehyde (11.07 g, 89 mmol) in DMF (200 mL) was added K2CO3 (13.33 g, 96 mmol). The mixture was heated at 140° C. for 4 h. After cooling to room temperature, the mixture was poured into of ice water (300 mL), and left stand overnight. The solid was collected by filtration, washed with water, re-dissolved in EA (200 mL) and washed with brine (100 mL). The organic phase was dried with sodium sulfate, filtered and concentrated to afford the title compound (17 g, 75 mmol, 84% yield) as yellow solid. LCMS: rt=1.52 min, [M+H+]=217

Workup

  1. temperatureAfter cooling to room temperature
  2. waitleft
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. dissolutionre-dissolved in EA (200 mL)
  6. washwashed with brine (100 mL)
  7. dry with materialThe organic phase was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8bddd63461a64eac9ef862a21424f725
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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